organic compounds Acta Crystallographica Section E
Experimental
Structure Reports Online
Crystal data
ISSN 1600-5368
2,9,16,23-Tetrakis(1-methylethyl)5,6,11,12,13,14,19,20,25,26,27,28dodecadehydrotetrabenzo[a,e,k,o]cycloeicosene1 Theshini Perera, Frank R. Fronczek* and Steven F. Watkins Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA Correspondence e-mail:
[email protected] Received 25 October 2011; accepted 15 November 2011 Key indicators: single-crystal X-ray study; T = 90 K, P = 0.0 kPa; mean (C–C) = ˚ ; R factor = 0.049; wR factor = 0.127; data-to-parameter ratio = 18.5. 0.002 A
The title compound, C48H40, is a tetraisopropyl-substituted polyannulenoenyne. The unsubstituted polyannulenoenyne, C36H16 (CSD: RICVEE; CAS: 186494-87-1), has quasi-D2 (222) symmetry, as determined by least-squares fit (excluding H atoms) to a model optimized in D2 symmetry by molecular ˚ ). The least-squares fits mechanics (r.m.s. deviation = 0.239 A of 36 common C atoms of the title compound (at 90 K) to the parent (at 295 K) and to the optimized model show r.m.s. ˚ , respectively. deviations of 0.419 and 0.426 A
C48H40 Mr = 616.8 Monoclinic, P21 =c ˚ a = 18.0007 (4) A ˚ b = 12.5083 (3) A ˚ c = 16.0674 (4) A = 91.004 (1)
˚3 V = 3617.15 (15) A Z=4 Mo K radiation = 0.06 mm 1 T = 90 K 0.45 0.30 0.30 mm
Data collection Nonius KappaCCD diffractometer Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997) Tmin = 0.972, Tmax = 0.981
13998 measured reflections 8186 independent reflections 5354 reflections with I > 2(I) Rint = 0.035
Refinement R[F 2 > 2(F 2)] = 0.049 wR(F 2) = 0.127 S = 1.02 8186 reflections
442 parameters H-atom parameters constrained ˚ 3 max = 0.25 e A ˚ 3 min = 0.28 e A
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: IDEAL (Gould et al., 1988) and WinGX (Farrugia, 1999).
The purchase of the diffractometer was made possible by Grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. We are grateful to Professor Adam Matzger for providing the sample.
Related literature For a description of the Cambridge Structural Database, see: Allen (2002). For the synthesis and a related structure, see: Boese et al. (1997). For molecular mechanics software, see: Cambridgesoft (2010).
1
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2194).
References Allen, F. H. (2002). Acta Cryst. B58, 380–388. Boese, R., Matzger, A. J. & Vollhardt, K. P. C. (1997). J. Am. Chem. Soc. 119, 2052–2053. Cambridgesoft (2010). Chem3DPro. Cambridgesoft Corporation, Cambridge, MA, USA. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Gould, R. O., Moulden, N., Taylor, N. & Taylor, P. (1988). IDEAL. Department of Chemistry, University of Edinburgh, Scotland. Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
CAS 186494-88-2.
Acta Cryst. (2011). E67, o3493
doi:10.1107/S1600536811048604
Perera et al.
o3493
supplementary materials
supplementary materials Acta Cryst. (2011). E67, o3493
[ doi:10.1107/S1600536811048604 ]
2,9,16,23-Tetrakis(1-methylethyl)-5,6,11,12,13,14,19,20,25,26,27,28dodecadehydrotetrabenzo[a,e,k,o]cycloeicosene T. Perera, F. R. Fronczek and S. F. Watkins Comment The title compound, C48H40, is a tetraisopropyl-substituted polyannulenoenyne and its structure was determined at 90 K. The 295 K structure of the unsubstituted parent annulene, C36H16, was previously determined by Boese et al. (1997; CSD: RICVEE, Allen, 2002; CAS: 186494–87-1), and is of quasi-D2 (222) symmetry, as determined by least-squares fit (Gould et al., 1988; δr.m.s. = 0.239 Å) of all 36 common carbon atoms of the parent to a model of C36H16 optimized in D2 symmetry by molecular mechanics (Cambridgesoft, 2010). Reasonable agreements result from the same least-squares fit of the title compound (at 90 K) to the parent (δr.m.s. =0.419 Å) and to the optimized model (δr.m.s. = 0.426 Å). The six C≡C triple bond distances are all experimentally equal, falling in the narrow range 1.203 (2) - 1.206 (2) Å, while the C–C bonds linking the triple bonds have length C16—C17 1.370 (2) and C34—C35 1.377 (2) Å. The acetylenic bridges are slightly bowed outward, with C–C≡C angles in the range 177.59 (18) - 179.17 (18)° for the butadiyne bridges and in the range 174.43 (17) - 176.80 (17)° for the acetylene bridges. Distances between the following bond centroids provide a measure of overall molecular dimensions: C16—C17 to C34—C35 = 3.341 (2) Å, C7 ≡C8 to C25 ≡C26 = 7.650 (2) Å. Experimental The preparation of the title compound has been described by Boese et al. (1997). Crystals were grown by slow evaporation from dichloromethane and deuterochloroform. Refinement All H atoms were placed in calculated positions guided by difference maps. The C—H bond distances were constrained to the range from 0.95 to 1.0 Å, depending on C atom type, and Uiso= 1.2Ueq (1.5 for methyl groups), thereafter refined as riding. A torsional parameter was refined for each methyl group.
Figures
Fig. 1. View of the title compound showing 50% probability displacement ellipsoids.
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supplementary materials 7,16,25,34-tetrakis(propan-2-yl)pentacyclo[30.4.0.04,9.014,19.022,27] hexatriaconta1(32),4,6,8,14 (19),15,17,22,24,26,33,35-dodecaen- 2,10,12,20,28,30-hexayne Crystal data C48H40
F(000) = 1312
Mr = 616.8
Dx = 1.133 Mg m−3
Monoclinic, P21/c
Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc a = 18.0007 (4) Å
Cell parameters from 7618 reflections θ = 2.6–29.1°
b = 12.5083 (3) Å
µ = 0.06 mm−1 T = 90 K Prism, golden yellow
c = 16.0674 (4) Å β = 91.004 (1)° V = 3617.15 (15) Å3 Z=4
0.45 × 0.30 × 0.30 mm
Data collection Nonius KappaCCD diffractometer Radiation source: sealed tube horizonally mounted graphite crystal Detector resolution: 9 pixels mm-1 CCD rotation images, thick slices scans Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997) Tmin = 0.972, Tmax = 0.981
8186 independent reflections 5354 reflections with I > 2σ(I) Rint = 0.035 θmax = 28.9°, θmin = 2.8° h = −23→23 k = −16→14 l = −19→20
13998 measured reflections
Refinement Refinement on F2
Secondary atom site location: difference Fourier map
Least-squares matrix: full
Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049
H-atom parameters constrained
wR(F2) = 0.127
w = 1/[σ2(Fo2) + (0.0543P)2 + 1.183P] where P = (Fo2 + 2Fc2)/3
S = 1.02
(Δ/σ)max = 0.001
8186 reflections
Δρmax = 0.25 e Å−3
442 parameters
Δρmin = −0.28 e Å−3
0 restraints 0 constraints Primary atom site location: structure-invariant direct methods
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Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0017 (4)
supplementary materials Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) C1 C2 H2 C3 C4 H4 C5 H5 C6 C7 C8 C9 C10 H10 C11 H11 C12 C13 H13 C14 C15 C16 C17 C18 C19 C20 H20 C21 C22 H22 C23 H23 C24 C25 C26 C27 C28 H28
x
y
z
Uiso*/Ueq
0.34021 (9) 0.37458 (9) 0.3986 0.37425 (9) 0.33685 (9) 0.3348 0.30274 (9) 0.2781 0.30408 (9) 0.26840 (9) 0.23760 (9) 0.20160 (8) 0.20544 (9) 0.2289 0.17525 (9) 0.1793 0.13916 (9) 0.13314 (9) 0.1073 0.16417 (8) 0.15945 (9) 0.15709 (9) 0.15610 (9) 0.15587 (9) 0.15470 (9) 0.12070 (9) 0.0977 0.11988 (9) 0.15239 (10) 0.1519 0.18519 (9) 0.2058 0.18827 (9) 0.22660 (9) 0.25924 (9) 0.29570 (9) 0.29559 (9) 0.2728
0.67572 (12) 0.65496 (13) 0.5882 0.72994 (13) 0.82602 (13) 0.8774 0.84840 (13) 0.9149 0.77426 (12) 0.79587 (12) 0.80786 (12) 0.81294 (12) 0.90410 (13) 0.9669 0.90345 (13) 0.9658 0.81390 (13) 0.72469 (12) 0.6636 0.72248 (12) 0.62679 (12) 0.54517 (12) 0.45239 (12) 0.36996 (13) 0.27065 (12) 0.26396 (13) 0.3257 0.16932 (13) 0.07952 (13) 0.0136 0.08346 (13) 0.0204 0.17957 (12) 0.18904 (12) 0.20612 (12) 0.23181 (12) 0.16136 (14) 0.0932
−0.03559 (9) −0.11163 (9) −0.1196 −0.17553 (9) −0.16283 (9) −0.2064 −0.08857 (9) −0.0816 −0.02347 (9) 0.05395 (9) 0.11918 (9) 0.19792 (9) 0.24814 (10) 0.2282 0.32691 (10) 0.3604 0.35838 (9) 0.30736 (9) 0.3267 0.22813 (9) 0.17971 (9) 0.13983 (9) 0.09457 (9) 0.05588 (9) 0.01184 (9) −0.06716 (9) −0.0905 −0.11210 (10) −0.07467 (10) −0.104 0.00358 (10) 0.0275 0.04787 (9) 0.12662 (10) 0.19125 (10) 0.26867 (9) 0.33603 (10) 0.3298
0.0209 (3) 0.0230 (4) 0.028* 0.0239 (4) 0.0250 (4) 0.03* 0.0240 (4) 0.029* 0.0211 (3) 0.0221 (3) 0.0221 (3) 0.0215 (3) 0.0264 (4) 0.032* 0.0269 (4) 0.032* 0.0223 (3) 0.0208 (3) 0.025* 0.0198 (3) 0.0216 (3) 0.0215 (3) 0.0223 (3) 0.0232 (3) 0.0219 (3) 0.0237 (4) 0.028* 0.0256 (4) 0.0300 (4) 0.036* 0.0281 (4) 0.034* 0.0230 (3) 0.0235 (4) 0.0240 (4) 0.0228 (3) 0.0289 (4) 0.035*
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supplementary materials C29 H29 C30 C31 H31 C32 C33 C34 C35 C36 C37 H37 C38 H38A H38B H38C C39 H39A H39B H39C C40 H40 C41 H41A H41B H41C C42 H42A H42B H42C C43 H43 C44 H44A H44B H44C C45 H45A H45B H45C C46 H46 C47 H47A H47B H47C C48 H48A H48B
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0.32799 (9) 0.3269 0.36228 (9) 0.36368 (9) 0.387 0.33159 (9) 0.33649 (9) 0.34108 (9) 0.34333 (9) 0.34260 (9) 0.41549 (10) 0.3804 0.48096 (10) 0.4631 0.5045 0.5173 0.44060 (12) 0.4774 0.4628 0.3977 0.10830 (9) 0.1495 0.08181 (10) 0.0394 0.0668 0.1222 0.04634 (10) 0.0642 0.0309 0.0039 0.08507 (10) 0.1231 0.06418 (11) 0.0244 0.0471 0.1077 0.01798 (11) 0.0326 0.0001 −0.0217 0.40087 (9) 0.3752 0.39803 (11) 0.4255 0.4205 0.3462 0.48084 (12) 0.4818 0.5057
0.18895 (13) 0.1394 0.28784 (13) 0.35806 (13) 0.4257 0.33165 (12) 0.40474 (12) 0.46519 (12) 0.53578 (12) 0.59846 (12) 0.71348 (14) 0.7324 0.79092 (15) 0.8642 0.7847 0.7735 0.59924 (15) 0.5793 0.5934 0.5512 0.81729 (13) 0.8419 0.70983 (14) 0.685 0.7177 0.6576 0.89944 (14) 0.9687 0.9062 0.8764 0.16014 (14) 0.1266 0.26707 (15) 0.3003 0.2555 0.3142 0.08507 (15) 0.0164 0.0736 0.1171 0.31230 (14) 0.27 0.42839 (15) 0.4716 0.4367 0.4522 0.2742 (2) 0.1969 0.2906
0.41168 (10) 0.4564 0.42378 (9) 0.35677 (9) 0.3636 0.27927 (9) 0.21094 (9) 0.15295 (9) 0.08726 (9) 0.03031 (9) −0.25636 (10) −0.303 −0.26042 (11) −0.2528 −0.3148 −0.2163 −0.27061 (12) −0.2277 −0.3257 −0.2676 0.44585 (9) 0.4838 0.47865 (10) 0.4449 0.5367 0.4755 0.45132 (10) 0.4315 0.5093 0.4167 −0.19909 (10) −0.2354 −0.23850 (10) −0.2067 −0.296 −0.2381 −0.19878 (11) −0.1741 −0.256 −0.166 0.50654 (9) 0.5504 0.53199 (11) 0.492 0.5876 0.5329 0.50436 (13) 0.4948 0.5576
0.0286 (4) 0.034* 0.0238 (4) 0.0225 (3) 0.027* 0.0213 (3) 0.0224 (3) 0.0233 (4) 0.0232 (4) 0.0228 (3) 0.0301 (4) 0.036* 0.0377 (5) 0.057* 0.057* 0.057* 0.0442 (5) 0.066* 0.066* 0.066* 0.0261 (4) 0.031* 0.0315 (4) 0.047* 0.047* 0.047* 0.0308 (4) 0.046* 0.046* 0.046* 0.0317 (4) 0.038* 0.0359 (4) 0.054* 0.054* 0.054* 0.0392 (5) 0.059* 0.059* 0.059* 0.0294 (4) 0.035* 0.0393 (5) 0.059* 0.059* 0.059* 0.0581 (7) 0.087* 0.087*
supplementary materials H48C
0.5066
0.3106
0.4592
0.087*
Atomic displacement parameters (Å2) C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35 C36 C37 C38 C39 C40 C41 C42 C43
U11 0.0265 (8) 0.0273 (9) 0.0281 (9) 0.0298 (9) 0.0274 (9) 0.0240 (8) 0.0268 (8) 0.0272 (8) 0.0250 (8) 0.0321 (9) 0.0329 (9) 0.0232 (8) 0.0251 (8) 0.0230 (8) 0.0280 (9) 0.0271 (9) 0.0285 (9) 0.0266 (9) 0.0259 (8) 0.0274 (9) 0.0278 (9) 0.0384 (10) 0.0354 (10) 0.0263 (8) 0.0300 (9) 0.0314 (9) 0.0271 (9) 0.0365 (10) 0.0359 (10) 0.0259 (8) 0.0251 (8) 0.0254 (8) 0.0269 (9) 0.0289 (9) 0.0292 (9) 0.0267 (9) 0.0373 (10) 0.0444 (11) 0.0608 (13) 0.0319 (9) 0.0420 (11) 0.0346 (10) 0.0375 (10)
U22 0.0179 (8) 0.0204 (8) 0.0263 (9) 0.0244 (9) 0.0193 (8) 0.0198 (8) 0.0158 (8) 0.0154 (8) 0.0194 (8) 0.0175 (8) 0.0209 (9) 0.0218 (8) 0.0170 (8) 0.0162 (8) 0.0186 (8) 0.0190 (8) 0.0185 (8) 0.0218 (8) 0.0179 (8) 0.0210 (8) 0.0244 (9) 0.0209 (9) 0.0175 (8) 0.0213 (8) 0.0156 (8) 0.0163 (8) 0.0211 (8) 0.0219 (9) 0.0275 (9) 0.0255 (9) 0.0192 (8) 0.0191 (8) 0.0186 (8) 0.0188 (8) 0.0192 (8) 0.0196 (8) 0.0342 (10) 0.0346 (11) 0.0367 (11) 0.0263 (9) 0.0312 (10) 0.0300 (10) 0.0329 (10)
U33 0.0181 (7) 0.0212 (8) 0.0174 (8) 0.0208 (8) 0.0251 (8) 0.0196 (8) 0.0238 (8) 0.0237 (8) 0.0200 (8) 0.0296 (9) 0.0269 (9) 0.0220 (8) 0.0204 (8) 0.0200 (7) 0.0182 (8) 0.0186 (8) 0.0198 (8) 0.0212 (8) 0.0220 (8) 0.0228 (8) 0.0247 (8) 0.0306 (9) 0.0311 (9) 0.0214 (8) 0.0251 (8) 0.0243 (8) 0.0203 (8) 0.0283 (9) 0.0225 (8) 0.0202 (8) 0.0232 (8) 0.0194 (8) 0.0215 (8) 0.0221 (8) 0.0211 (8) 0.0221 (8) 0.0188 (8) 0.0346 (10) 0.0358 (10) 0.0203 (8) 0.0216 (8) 0.0278 (9) 0.0245 (9)
U12 −0.0032 (7) −0.0019 (7) −0.0052 (7) −0.0027 (7) 0.0011 (7) −0.0029 (7) −0.0017 (7) −0.0013 (7) 0.0021 (7) −0.0049 (7) −0.0021 (7) 0.0043 (7) 0.0016 (7) 0.0024 (7) 0.0013 (7) 0.0000 (7) 0.0002 (7) 0.0004 (7) −0.0006 (7) 0.0024 (7) 0.0020 (7) 0.0025 (8) 0.0039 (7) −0.0015 (7) −0.0001 (7) −0.0020 (7) 0.0009 (7) −0.0067 (8) −0.0015 (8) 0.0054 (7) 0.0006 (7) 0.0030 (7) −0.0006 (7) −0.0002 (7) −0.0002 (7) −0.0008 (7) −0.0040 (8) −0.0041 (9) −0.0074 (10) 0.0034 (8) 0.0035 (8) 0.0053 (8) 0.0040 (8)
U13 −0.0015 (6) −0.0010 (6) −0.0001 (6) −0.0001 (7) 0.0005 (7) 0.0001 (6) −0.0011 (7) −0.0002 (7) 0.0001 (6) 0.0045 (7) 0.0035 (7) 0.0008 (6) 0.0001 (6) −0.0019 (6) 0.0019 (6) −0.0001 (6) −0.0009 (6) 0.0004 (6) 0.0025 (6) −0.0004 (7) −0.0013 (7) −0.0061 (8) −0.0051 (7) −0.0004 (6) 0.0020 (7) 0.0015 (7) 0.0001 (6) −0.0015 (7) 0.0010 (7) 0.0014 (6) 0.0002 (6) 0.0013 (6) −0.0021 (6) −0.0011 (7) 0.0002 (7) −0.0001 (7) 0.0036 (7) 0.0157 (8) 0.0218 (9) 0.0017 (7) 0.0060 (7) 0.0055 (7) −0.0054 (7)
U23 0.0005 (6) −0.0032 (6) −0.0020 (6) 0.0048 (7) 0.0019 (6) −0.0008 (6) 0.0006 (6) −0.0001 (6) −0.0015 (6) −0.0040 (7) −0.0084 (7) −0.0030 (6) −0.0001 (6) −0.0026 (6) 0.0015 (6) 0.0024 (6) −0.0003 (6) 0.0002 (7) −0.0043 (6) −0.0017 (6) −0.0062 (7) −0.0100 (7) −0.0039 (7) −0.0019 (6) −0.0015 (6) 0.0011 (6) 0.0004 (6) 0.0037 (7) 0.0076 (7) −0.0001 (7) −0.0013 (6) 0.0002 (6) −0.0030 (7) −0.0025 (7) −0.0016 (6) −0.0035 (7) −0.0022 (7) −0.0031 (8) −0.0126 (8) −0.0054 (7) 0.0005 (7) −0.0044 (7) −0.0093 (7)
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supplementary materials C44 C45 C46 C47 C48
0.0410 (11) 0.0453 (11) 0.0348 (10) 0.0482 (12) 0.0526 (14)
0.0415 (11) 0.0364 (11) 0.0362 (10) 0.0394 (11) 0.0865 (18)
0.0251 (9) 0.0356 (10) 0.0172 (8) 0.0299 (10) 0.0347 (11)
0.0019 (9) −0.0001 (9) 0.0052 (8) −0.0024 (9) 0.0291 (13)
−0.0056 (8) −0.0124 (9) −0.0012 (7) −0.0119 (8) −0.0175 (10)
−0.0020 (8) −0.0080 (8) −0.0009 (7) −0.0046 (8) −0.0187 (11)
Geometric parameters (Å, °) C1—C2 C1—C6 C1—C36 C2—C3 C2—H2 C3—C4 C3—C37 C4—C5 C4—H4 C5—C6 C5—H5 C6—C7 C7—C8 C8—C9 C9—C10 C9—C14 C10—C11 C10—H10 C11—C12 C11—H11 C12—C13 C12—C40 C13—C14 C13—H13 C14—C15 C15—C16 C16—C17 C17—C18 C18—C19 C19—C20 C19—C24 C20—C21 C20—H20 C21—C22 C21—C43 C22—C23 C22—H22 C23—C24 C23—H23 C24—C25 C25—C26
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1.403 (2) 1.409 (2) 1.434 (2) 1.391 (2) 0.95 1.394 (2) 1.521 (2) 1.380 (2) 0.95 1.398 (2) 0.95 1.436 (2) 1.204 (2) 1.433 (2) 1.398 (2) 1.408 (2) 1.386 (2) 0.95 1.394 (2) 0.95 1.388 (2) 1.521 (2) 1.399 (2) 0.95 1.429 (2) 1.206 (2) 1.370 (2) 1.204 (2) 1.430 (2) 1.402 (2) 1.409 (2) 1.386 (2) 0.95 1.398 (2) 1.526 (2) 1.381 (2) 0.95 1.398 (2) 0.95 1.436 (2) 1.203 (2)
C29—C30 C29—H29 C30—C31 C30—C46 C31—C32 C31—H31 C32—C33 C33—C34 C34—C35 C35—C36 C37—C39 C37—C38 C37—H37 C38—H38A C38—H38B C38—H38C C39—H39A C39—H39B C39—H39C C40—C42 C40—C41 C40—H40 C41—H41A C41—H41B C41—H41C C42—H42A C42—H42B C42—H42C C43—C44 C43—C45 C43—H43 C44—H44A C44—H44B C44—H44C C45—H45A C45—H45B C45—H45C C46—C47 C46—C48 C46—H46 C47—H47A
1.394 (2) 0.95 1.390 (2) 1.520 (2) 1.403 (2) 0.95 1.432 (2) 1.204 (2) 1.377 (2) 1.205 (2) 1.517 (3) 1.528 (2) 1 0.98 0.98 0.98 0.98 0.98 0.98 1.520 (2) 1.523 (2) 1 0.98 0.98 0.98 0.98 0.98 0.98 1.524 (2) 1.530 (3) 1 0.98 0.98 0.98 0.98 0.98 0.98 1.510 (2) 1.517 (3) 1 0.98
supplementary materials C26—C27 C27—C28 C27—C32 C28—C29 C28—H28
1.433 (2) 1.396 (2) 1.415 (2) 1.383 (2) 0.95
C47—H47B C47—H47C C48—H48A C48—H48B C48—H48C
0.98 0.98 0.98 0.98 0.98
C2—C1—C6 C2—C1—C36 C6—C1—C36 C3—C2—C1 C3—C2—H2 C1—C2—H2 C2—C3—C4 C2—C3—C37 C4—C3—C37 C5—C4—C3 C5—C4—H4 C3—C4—H4 C4—C5—C6 C4—C5—H5 C6—C5—H5 C5—C6—C1 C5—C6—C7 C1—C6—C7 C8—C7—C6 C7—C8—C9 C10—C9—C14 C10—C9—C8 C14—C9—C8 C11—C10—C9 C11—C10—H10 C9—C10—H10 C10—C11—C12 C10—C11—H11 C12—C11—H11 C13—C12—C11 C13—C12—C40 C11—C12—C40 C12—C13—C14 C12—C13—H13 C14—C13—H13 C13—C14—C9 C13—C14—C15 C9—C14—C15 C16—C15—C14 C15—C16—C17 C18—C17—C16 C17—C18—C19 C20—C19—C24 C20—C19—C18
119.60 (13) 120.68 (14) 119.71 (13) 121.45 (15) 119.3 119.3 117.98 (14) 122.91 (15) 119.06 (14) 121.64 (14) 119.2 119.2 120.69 (15) 119.7 119.7 118.62 (14) 121.42 (14) 119.95 (13) 176.25 (16) 175.33 (17) 118.40 (14) 121.83 (14) 119.70 (14) 120.41 (15) 119.8 119.8 121.90 (14) 119 119 117.63 (14) 122.84 (14) 119.53 (14) 121.67 (14) 119.2 119.2 119.93 (14) 119.39 (14) 120.64 (13) 178.34 (17) 178.73 (18) 178.88 (18) 178.44 (17) 120.06 (14) 120.17 (14)
C31—C32—C33 C27—C32—C33 C34—C33—C32 C33—C34—C35 C36—C35—C34 C35—C36—C1 C39—C37—C3 C39—C37—C38 C3—C37—C38 C39—C37—H37 C3—C37—H37 C38—C37—H37 C37—C38—H38A C37—C38—H38B H38A—C38—H38B C37—C38—H38C H38A—C38—H38C H38B—C38—H38C C37—C39—H39A C37—C39—H39B H39A—C39—H39B C37—C39—H39C H39A—C39—H39C H39B—C39—H39C C42—C40—C12 C42—C40—C41 C12—C40—C41 C42—C40—H40 C12—C40—H40 C41—C40—H40 C40—C41—H41A C40—C41—H41B H41A—C41—H41B C40—C41—H41C H41A—C41—H41C H41B—C41—H41C C40—C42—H42A C40—C42—H42B H42A—C42—H42B C40—C42—H42C H42A—C42—H42C H42B—C42—H42C C44—C43—C21 C44—C43—C45
120.00 (14) 120.34 (13) 179.17 (18) 177.59 (18) 177.59 (18) 177.89 (17) 114.04 (14) 111.02 (15) 109.82 (13) 107.2 107.2 107.2 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 110.63 (13) 110.00 (14) 114.63 (13) 107.1 107.1 107.1 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 114.14 (14) 110.55 (15)
sup-7
supplementary materials C24—C19—C18 C21—C20—C19 C21—C20—H20 C19—C20—H20 C20—C21—C22 C20—C21—C43 C22—C21—C43 C23—C22—C21 C23—C22—H22 C21—C22—H22 C22—C23—C24 C22—C23—H23 C24—C23—H23 C23—C24—C19 C23—C24—C25 C19—C24—C25 C26—C25—C24 C25—C26—C27 C28—C27—C32 C28—C27—C26 C32—C27—C26 C29—C28—C27 C29—C28—H28 C27—C28—H28 C28—C29—C30 C28—C29—H29 C30—C29—H29 C31—C30—C29 C31—C30—C46 C29—C30—C46 C30—C31—C32 C30—C31—H31 C32—C31—H31 C31—C32—C27
119.78 (13) 121.53 (15) 119.2 119.2 117.49 (14) 122.80 (15) 119.72 (14) 122.16 (15) 118.9 118.9 120.46 (15) 119.8 119.8 118.25 (14) 122.27 (15) 119.44 (14) 174.43 (17) 176.80 (17) 118.09 (14) 121.65 (15) 120.24 (14) 121.18 (15) 119.4 119.4 121.52 (15) 119.2 119.2 117.81 (14) 122.41 (15) 119.65 (14) 121.73 (15) 119.1 119.1 119.64 (14)
C21—C43—C45 C44—C43—H43 C21—C43—H43 C45—C43—H43 C43—C44—H44A C43—C44—H44B H44A—C44—H44B C43—C44—H44C H44A—C44—H44C H44B—C44—H44C C43—C45—H45A C43—C45—H45B H45A—C45—H45B C43—C45—H45C H45A—C45—H45C H45B—C45—H45C C47—C46—C48 C47—C46—C30 C48—C46—C30 C47—C46—H46 C48—C46—H46 C30—C46—H46 C46—C47—H47A C46—C47—H47B H47A—C47—H47B C46—C47—H47C H47A—C47—H47C H47B—C47—H47C C46—C48—H48A C46—C48—H48B H48A—C48—H48B C46—C48—H48C H48A—C48—H48C H48B—C48—H48C
110.78 (14) 107 107 107 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 110.17 (17) 114.42 (14) 109.62 (14) 107.5 107.5 107.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5
C6—C1—C2—C3 C36—C1—C2—C3 C1—C2—C3—C4 C1—C2—C3—C37 C2—C3—C4—C5 C37—C3—C4—C5 C3—C4—C5—C6 C4—C5—C6—C1 C4—C5—C6—C7 C2—C1—C6—C5 C36—C1—C6—C5 C2—C1—C6—C7 C36—C1—C6—C7 C14—C9—C10—C11 C8—C9—C10—C11
0.4 (2) −178.54 (15) −1.7 (2) 175.55 (15) 1.8 (2) −175.55 (15) −0.6 (2) −0.7 (2) −179.51 (15) 0.8 (2) 179.77 (14) 179.63 (14) −1.4 (2) 2.2 (2) −174.65 (15)
C22—C23—C24—C25 C20—C19—C24—C23 C18—C19—C24—C23 C20—C19—C24—C25 C18—C19—C24—C25 C32—C27—C28—C29 C26—C27—C28—C29 C27—C28—C29—C30 C28—C29—C30—C31 C28—C29—C30—C46 C29—C30—C31—C32 C46—C30—C31—C32 C30—C31—C32—C27 C30—C31—C32—C33 C28—C27—C32—C31
−175.30 (16) −1.3 (2) 179.13 (15) 176.40 (15) −3.2 (2) 1.5 (2) −176.98 (16) −0.2 (3) −0.7 (2) −176.65 (15) 0.3 (2) 176.14 (14) 1.0 (2) −177.81 (15) −1.9 (2)
sup-8
supplementary materials C9—C10—C11—C12 C10—C11—C12—C13 C10—C11—C12—C40 C11—C12—C13—C14 C40—C12—C13—C14 C12—C13—C14—C9 C12—C13—C14—C15 C10—C9—C14—C13 C8—C9—C14—C13 C10—C9—C14—C15 C8—C9—C14—C15 C24—C19—C20—C21 C18—C19—C20—C21 C19—C20—C21—C22 C19—C20—C21—C43 C20—C21—C22—C23 C43—C21—C22—C23 C21—C22—C23—C24 C22—C23—C24—C19
−1.1 (3) −1.1 (2) 178.95 (15) 2.1 (2) −177.86 (14) −1.0 (2) 177.02 (14) −1.2 (2) 175.78 (14) −179.21 (14) −2.3 (2) −0.8 (2) 178.76 (15) 1.8 (2) −178.43 (15) −0.8 (3) 179.47 (16) −1.3 (3) 2.3 (2)
C26—C27—C32—C31 C28—C27—C32—C33 C26—C27—C32—C33 C2—C3—C37—C39 C4—C3—C37—C39 C2—C3—C37—C38 C4—C3—C37—C38 C13—C12—C40—C42 C11—C12—C40—C42 C13—C12—C40—C41 C11—C12—C40—C41 C20—C21—C43—C44 C22—C21—C43—C44 C20—C21—C43—C45 C22—C21—C43—C45 C31—C30—C46—C47 C29—C30—C46—C47 C31—C30—C46—C48 C29—C30—C46—C48
176.64 (15) 176.94 (15) −4.5 (2) 14.4 (2) −168.35 (16) −110.89 (18) 66.3 (2) −115.35 (17) 64.6 (2) 9.7 (2) −170.28 (15) 10.6 (2) −169.67 (16) −114.94 (18) 64.8 (2) 36.4 (2) −147.78 (16) −87.9 (2) 87.9 (2)
sup-9
supplementary materials Fig. 1
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